Methods for producing an isoxazoline compound from a 1,3-bis(substituted phenyl)-3-substituted-2-propen-1-one compound and hydroxylamine as raw materials have been known in, for example, Non-patent Documents 1 to 6.
Several methods for producing a 1,3-bis(substituted phenyl)-3-substituted-3-hydroxypropan-1-one compound from an aromatic ketone compound and a substituted acetophenone compound as starting raw materials have been known (for example, Patent Document 1 and Non-patent Documents 7 to 15).
Moreover, methods for producing a 1,3-bis(substituted phenyl)-3-substituted-2-propen-1-one compound from a 1,3-bis(substituted phenyl)-3-substituted-3-hydroxypropan-1-one compound as a raw material have been known in, for example, Non-patent Documents 10 and 11.
Furthermore, methods for producing a 1,3-bis(substituted phenyl)-3-substituted-2-propen-1-one compound from an aromatic ketone compound and a substituted acetophenone compound as starting raw materials in one step have been known in, for example, Non-patent Documents 18 to 20.
[Patent Document 1]
    WO 2007/074789 pamphlet[Non-Patent Document 1]    Farmaco, Edizione Scientifica (1971), 591-596[Non-Patent Document 2]    Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie (1977), 443-446[Non-Patent Document 3]    Bulletin des Societes Chimiques Beiges (1987), 293-302[Non-Patent Document 4]    Journal of Heterocyclic Chemistry (1998), 989-990[Non-Patent Document 5]    Synthetic Communication (1999), 3237-3250[Non-Patent Document 6]    Archives of Pharmacal Research (2004), 885-892[Non-Patent Document 7]    Zhurnal Organicheskoi Khimii, vol. 26, No. 10, 2205-2208 (1990)[Non-Patent Document 8]    Journal of Fluorine Chemistry, vol. 113, 105-109 (2002)[Non-Patent Document 9]    Organic Letters vol. 7, No. 22, 5103-5105 (2005)[Non-Patent Document 10]    Journal of Organic Chemistry, vol. 71, 3822-3828 (2006)[Non-Patent Document 11]    Chinese Journal of Chemistry, vol. 23, 584-588 (2005)[Non-Patent Document 12]    Synthesis, No. 17, 2901-2905 (2005)[Non-Patent Document 13]    Tetrahedron Letters, vol. 38, 8727-8730 (1997)[Non-Patent Document 14]    Tetrahedron, vol. 58, 8263-8268 (2002)[Non-Patent Document 15]    Organic Process Research and Development, vol. 8, 18-21 (2004)[Non-Patent Document 16]    Tetrahedron, Vol. 58, No. 39, 7775-7780 (2002)[Non-Patent Document 17]    Tetrahedron Letters, vol. 46, 8913-8915 (2005)[Non-Patent Document 18]    Journal of Organic Chemistry, Vol. 71, No. 9, 3545-3555 (2006)[Non-Patent Document 19]    Journal of Fluorine Chemistry, Vol. 125 No. 1, 91-94 (2004)[Non-Patent Document 20]    Journal of Molecular Catalysis A: Chemical, Vol. 181, 179-187 (2002)